Entertainment
15.8k voters

The Funniest '90s Movies

Updated January 21, 2021 281.3k votes 15.8k voters 633.1k views252 items

List RulesVote up the most hilarious comedies released between 1990 and 1999.

Here are the funniest 90s movies and the best comedies of the 1990s that are ready for your votes. Nineties nostalgia exists for a reason. One of the main reasons is the unforgettable  and classic comedies that came out in movie theaters. It is also why we still constantly replay them in our homes today. Thanks to the Zucker brothers, we got the Farrelly brothers (and thereby There's Something About Mary) while the Cohen Brothers furthered their epic '90s comedy filmography with The Big Lebowski. Adam Sandler became one of the richest actors in all of Hollywood history as a result of the 1990s. In fact, his popular '90s comedy movies Billy Madison and Happy Gilmore make up his production company name today: Happy Madison. And who can forget Austin Powers' catchphrases spreading like wildfire? Kevin Smith also had two slam dunks with Clerks and Dogma, while the David Spade-Chris Farley funny, unforgettable, onscreen duo did the same with Black Sheep and Tommy Boy.

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  • 1
    4,388
    1,549

    Happy Gilmore

    Adam Sandler, Ben Stiller

    Released1996

    Directed byDennis Dugan

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  • 2
    3,575
    1,673

    Ace Ventura: Pet Detective

    Jim Carrey, Courteney Cox

    Released1994

    Directed byTom Shadyac

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    #63 of 924 The All-Time Greatest Comedy Films#119 of 440 The Best Movies Of The 1990s

  • 3
    4,534
    2,214

    Dumb and Dumber

    Jim Carrey, Jeff Daniels

    Released1994

    Directed byPeter Farrelly, Bobby Farrelly

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  • 4
    4,078
    1,231

    Tommy Boy

    Dan Aykroyd, Rob Lowe

    Released1995

    Directed byPeter Segal

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    #175 of 451 The Best Movies For Guys#24 of 541 The Greatest Guilty Pleasure Movies

  • 5
    2,522
    1,153

    Friday

    Ice Cube, Meagan Good

    Released1995

    Directed byF. Gary Gray

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  • 6
    2,948
    1,373

    Billy Madison

    Adam Sandler, Steve Buscemi

    Released1995

    Directed byTamra Davis

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  • 7
    3,441
    1,729

    Mrs. Doubtfire

    Robin Williams, Pierce Brosnan

    Released1993

    Directed byChris Columbus, Chuck Jones

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  • 8
    2,728
    1,422

    My Cousin Vinny

    Marisa Tomei, Joe Pesci

    Released1992

    Directed byJonathan Lynn

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  • 9
    3,174
    1,621

    There's Something About Mary

    Cameron Diaz, Sarah Silverman

    Released1998

    Directed byPeter Farrelly, Bobby Farrelly

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  • 10
    2,807
    1,360

    The Waterboy

    Adam Sandler, Kathy Bates

    Released1998

    Directed byFrank Coraci

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    #7 of 141 The Best College Movies Ever#72 of 153 The Most Inspirational Sports Movies

  • 11
    3,271
    1,745

    Austin Powers: International Man of Mystery

    Elizabeth Hurley, Will Ferrell

    Released1997

    Directed byJay Roach

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    #31 of 73 The Greatest Movies To Watch Outside#7 of 122 Great Movies That Place In The '60s

  • 12
    3,183
    1,722

    Liar Liar

    Jim Carrey, Jennifer Tilly

    Released1997

    Directed byTom Shadyac

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    #18 of 91 The Funniest Movies About Family#6 of 27 Actual Lawyers Explain Which Legal Movies They Like The Best

  • 13
    3,109
    1,585

    Wayne's World

    Alice Cooper, Mike Myers

    Released1992

    Directed byPenelope Spheeris

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  • 14
    2,715
    1,428

    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

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    #17 of 126 The Funniest Movies Starring SNL Cast Members#8 of 315 Movies with the Best Soundtracks

  • 15
    3,181
    1,709

    American Pie

    Alyson Hannigan, Tara Reid

    Released1999

    Directed byChris Weitz, Paul Weitz

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  • 16
    2,133
    847

    The Sandlot

    James Earl Jones, Denis Leary

    Released1993

    Directed byDavid M. Evans

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  • 17
    3,515
    1,981

    Groundhog Day

    Bill Murray, Andie MacDowell

    Released1993

    Directed byHarold Ramis

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    #47 of 112 Movies That Need Sequels#218 of 306 The Greatest Movie Themes

  • 18
    2,385
    994

    Men in Black

    Will Smith, Tommy Lee Jones

    Released1997

    Directed byBarry Sonnenfeld

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  • 19
    2,337
    1,093

    Toy Story

    Tom Hanks, Tim Allen

    Released1995

    Directed byJohn Lasseter

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  • 20
    3,526
    2,164

    Home Alone

    Macaulay Culkin, Joe Pesci

    Released1990

    Directed byChris Columbus

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  • 21
    2,648
    1,419

    The Big Lebowski

    Julianne Moore, Jeff Bridges

    Released1998

    Directed byEthan Coen, Joel Coen

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  • 22
    2,434
    1,460

    Big Daddy

    Adam Sandler, Jon Stewart

    Released1999

    Directed byDennis Dugan

    More Big Daddy 

    #36 of 83 Great Movies That Take Place In Autumn#10 of 50 The Best Father-Son Movies Ever Made

  • 23
    2,061
    1,249

    Austin Powers: The Spy Who Shagged Me

    Elizabeth Hurley, Heather Graham

    Released1999

    Directed byJay Roach

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  • 24
    2,381
    1,321

    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

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  • 25
    1,237
    605

    A League of Their Own

    Madonna, Tom Hanks

    Released1992

    Directed byPenny Marshall

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    #7 of 302 The Best Movies Based On True Stories#3 of 12 Movies Where The Cast And Crew Disagreed About Its Meaning